Hydrochloric Acid → 2-Chloro-5-pyridinesulfonyl chloride

HRID 547336Notes

Reaction equation

HRID 547336 reaction equation
N([O-])=O.[Na+].[Cl:5][C:6]1[N:11]=[CH:10][C:9](N)=[CH:8][CH:7]=1.[S:13](=[O:15])=[O:14].O.[ClH:17]>C(O)(=O)C.[Cu](Cl)Cl>[Cl:5][C:6]1[N:11]=[CH:10][C:9]([S:13]([Cl:17])(=[O:15])=[O:14])=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1119Sulfur DioxideHCID 793055-Amino-2-chloropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 27927922-Chloro-5-pyridinesulfonyl chlorideYield 60.5%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolvent2×

Procedure

Sodium nitrite (3.45 g, 0.05 mol) was added portion wise to a stirred solution of 6-chloro-pyridin-3-ylamine (6.4 g, 0.05 mol) in acetic acid (56 ml) and HCl (conc) (9.92 ml) while maintaining the temperature below 15° C. This solution was then added drop wise to a stirred solution of sulfur dioxide (17.2 g, 0.27 mol), copper (II) chloride (1.85 g, 0.011 mol) and water (2.2 ml) in acetic acid (37 ml) at 5° C. The reaction mixture was allowed to warm to room temperature and poured over ice water and stirred for a further 15 min. The resultant precipitate was collected by filtration, washed with water and dried overnight in a vacuum oven to give 6-chloro-pyridine-3-sulfonyl chloride (6.41 g, 60.5% yield); (400 MHz; d6-DMSO) 8.54 (1H, d), 7.96 (1H, dd), 7.50 (1H, d).

Workup

  1. temperaturewhile maintaining the temperature below 15° C
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with water
  4. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-1ca2e3b5e7c044738f14da6ee0d30d5a
Source dataset
uspto-grants-2011_05
Patent number
US07939532B2

Reaction notes

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